Search Deals onWalpole Vacation Packages
Walpole Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Latchis Hotel
Price was $631, price is now $501 per person
$501
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.

Lincoln Inn & Gallery
Price was $1,266, price is now $718 per person
$718
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!
Reviewed on Nov 8, 2026

1846 Inn and Tavern
Price was $935, price is now $810 per person
$810
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026

Sinclair Inn Bed and Breakfast
Price was $611, price is now $531 per person
$531
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.

Solitude Village at Okemo by Vail Resorts
Price was $8,402, price is now $7,377 per person
$7,377
per person
Jan 6 - Jan 10
found 9 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Galaxy Bowl are located nearby.

Deerfield Valley Inn
Price was $864, price is now $779 per person
$779
per person
Dec 30 - Jan 3
found 17 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was $662, price is now $600 per person
$600
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Good hotel. Spacious rooms. Offered many choices for breakfast. Gym was too small.
Reviewed on Nov 11, 2026

Mountain Lodge at Okemo, A Vail Resorts Property
Price was $1,135, price is now $1,041 per person
$1,041
per person
Jan 6 - Jan 10
found 9 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Walpole Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Walpole Vacation Packages 5-7 Night Stays
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